Basic Rules of Boot Season

It is boot season! Whether you are dusting off your trusty leather knee highs or going on a hunt for this year’s new shoe closet addition, if you’re a girl who loves playing dress up like me, you probably are doing so all giddy in excitement. Boots add a great tough-girl dimension to any outfit and is both built to be chic and comfy.

With the number of different styles for ladies boots out there, it is easy to get confused with what to wear with which outfit. To save you hours of trying boots on and going “does this look right?!”, read through this basic boot style guide.

Wearing tall boots? Fit is everything. Try loose equestrian pairs or a slim pair that is snug but not tight around your calves. Never try to push your calves in if they’re too slim for  your legs. Seeing jeans or calves struggling at the edge of your boot is a no-no. Tall boots will never look good under loose fitting or flared pants. They are best worn with tight jeans and or tights and leggings.

Love the skirt and boot look? Here’s what works best. Tall boots with a skirt or dress whose hem is just a few inches above the top of the boot, and if you are going shorter, wear with tights. Ankle boots are best with a skirts and dresses above the knee. If you go longer you can risk looking matronly and frumpy. 

Ankle boots with mid length skirts and capris is dangerous. Unless you are tall and modelesque, this is a risky pairing as it can make you look shorter.

Try not to wear uggs unless you are sure that it is a casual affair.  Uggs are the flipflops of boots. It is the kind of thing you don’t want to wear to good establishments. If you are going for the full comfort look, go ahead! Pair with a loose and warm pullover.

Mid-calf boots are unfortunately best on thin or long lean legs. They accentuate your calves. If you have bigger legs, go for a bit of height. Heel, wedge, platform… these are your best friends.

The more daring your boots, for example thigh highs, it is best paired with something simple and basic. Let your boots do the talking.

Make the most out of fall-winter fashion with your favorite pair/s. It’s one of the most fun times to play dress up, so go for it!